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Compound Detail

CHEMBL158570

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NC1=NC(c2cccc(Oc3ccc(Cl)cc3)c2)N(c2cccc(Cl)c2)C(N)=N1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL158570
Phase Preclinical
Structure Type MOL
InChI Key FWBIMLMZISAUKA-UHFFFAOYSA-N
5
Targets
15
Activities
2
Assay Types
0
PK Parameters
5
Publications
0
Known Names

Molecular Properties

426.3
MW (Da)
4.93
ALogP
6
HBA
2
HBD
89.2
PSA (Ų)
0.62
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H17Cl2N5O
MW 426.31
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness -0.83

Activity Summary

IC50 10 meas. best 6.41
Ki 5 meas. best 8.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 8.89 8.492 1.3 5
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 6.41 5.685 390.0 6
Plasmodium falciparum
CHEMBL364
 IC50 5.4 5.4 4000.0 1
KB
CHEMBL398
 IC50 5.16 5.16 7000.0 1
BC
CHEMBL613535
 IC50 5.0 5.0 10000.0 1
Vero
CHEMBL391
 IC50 4.51 4.51 31000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1.3 nM 8.89 Binding affinity towards wild-type dihydrofolate reductase of Plasmodium falcipa... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1.9 nM 8.72 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N DHFR) o... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 3.5 nM 8.46 Binding affinity towards mutant dihydrofolate reductase (A16V+S108T DHFR) of Pla... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 5.1 nM 8.29 Binding affinity towards mutant dihydrofolate reductase (C59R+S108N+I164L DHFR) ... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 8.0 nM 8.1 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N+I164L D... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 390.0 nM 6.41 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 2000.0 nM 5.7 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 2600.0 nM 5.58 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 3100.0 nM 5.51 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 3200.0 nM 5.5 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 3900.0 nM 5.41 In vitro anti-plasmodial activity against Plasmodium falciparum dihydrofolate re... 14736247
Plasmodium falciparum IC50 = 4000.0 nM 5.4 Antimicrobial activity against Plasmodium falciparum 20185316
KB IC50 = 7000.0 nM 5.16 In vitro cytotoxicity against Plasmodium falciparum infected KB cell line 14736247
BC IC50 = 10000.0 nM 5.0 In vitro cytotoxicity against Plasmodium falciparum infected BC cell line. 14736247
Vero IC50 = 31000.0 nM 4.51 In vitro cytotoxicity against Plasmodium falciparum infected vero cell line. 14736247

Literature References

PubMed DOI Target Context # Activities
14736247 10.1021/jm030165t Bifunctional dihydrofolate reductase-thymidylate synthase 15
14736247 10.1021/jm030165t Vero 5
14736247 10.1021/jm030165t KB 4
14736247 10.1021/jm030165t BC 3
20185316 10.1016/j.bmc.2010.01.068 Plasmodium falciparum 1

Data from ChEMBL 36 via Core Engine